Abstract
Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry,
with the potential to modulate physicochemical properties. Recent developments in
synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily
available, facilitating further study. This account reviews approaches to NH-sulfoximines,
with a focus on our contribution to the field. Starting from the development of catalytic
strategies involving transition metals, more sustainable metal-free processes have
been discovered. In particular, the use of hypervalent iodine reagents to mediate
NH-transfer to sulfoxides is described, along with an assessment of the substrate
scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines
is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic
evidence for the new procedures is included as well as relevant synthetic applications
that further exemplify the potential of these approaches.
1 Introduction
2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts
3 Metal-Free Strategies to Prepare NH-Sulfoximines
4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides
and Sulfides
5 Further Applications
6 Conclusion
Key words
NH-sulfoximines - N-transfer - hypervalent iodine - nitrenoids - catalysis
